CA2514047A1 - Spermicidal and/or antifungal composition and methods of using the same - Google Patents
Spermicidal and/or antifungal composition and methods of using the same Download PDFInfo
- Publication number
- CA2514047A1 CA2514047A1 CA002514047A CA2514047A CA2514047A1 CA 2514047 A1 CA2514047 A1 CA 2514047A1 CA 002514047 A CA002514047 A CA 002514047A CA 2514047 A CA2514047 A CA 2514047A CA 2514047 A1 CA2514047 A1 CA 2514047A1
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- CA
- Canada
- Prior art keywords
- compound
- iso
- hydrogen
- formula
- propyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 238000000034 method Methods 0.000 title claims abstract description 64
- 230000001150 spermicidal effect Effects 0.000 title claims abstract description 28
- 239000012871 anti-fungal composition Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 183
- 239000000203 mixture Substances 0.000 claims abstract description 72
- 230000002147 killing effect Effects 0.000 claims abstract description 38
- 241000233866 Fungi Species 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 73
- 239000001257 hydrogen Substances 0.000 claims description 66
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 53
- -1 hydroxymethyl ester Chemical class 0.000 claims description 39
- 150000002431 hydrogen Chemical group 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical class 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 25
- 239000003433 contraceptive agent Substances 0.000 claims description 23
- 230000002254 contraceptive effect Effects 0.000 claims description 16
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 13
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 13
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
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- 230000000855 fungicidal effect Effects 0.000 abstract description 12
- CINJODFGIBPBSD-UHFFFAOYSA-N 2,3,4,4a,4b,5-hexahydro-1h-indeno[2,1-b]pyridine Chemical class C1=CCC2C(CCCN3)C3=CC2=C1 CINJODFGIBPBSD-UHFFFAOYSA-N 0.000 abstract description 7
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
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- 230000000607 poisoning effect Effects 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 230000009933 reproductive health Effects 0.000 description 1
- 230000027272 reproductive process Effects 0.000 description 1
- 230000006965 reversible inhibition Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- DEIYFTQMQPDXOT-UHFFFAOYSA-N sildenafil citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 DEIYFTQMQPDXOT-UHFFFAOYSA-N 0.000 description 1
- 238000002603 single-photon emission computed tomography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000010009 steroidogenesis Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 210000001578 tight junction Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000002408 ulcerprotective effect Effects 0.000 description 1
- 210000003934 vacuole Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 229940094720 viagra Drugs 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/473—Quinolines; Isoquinolines ortho- or peri-condensed with carbocyclic ring systems, e.g. acridines, phenanthridines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/16—Masculine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/02—Local antiseptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Reproductive Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Orthopedics, Nursing, And Contraception (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/350,232 US7544696B2 (en) | 2003-01-24 | 2003-01-24 | Spermicidal and/or antifungal composition and methods of using the same |
| US10/350,232 | 2003-01-24 | ||
| PCT/US2004/000206 WO2004066934A2 (en) | 2003-01-24 | 2004-01-23 | Spermicidal and/or antifungal composition and methods of using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2514047A1 true CA2514047A1 (en) | 2004-08-12 |
Family
ID=32735516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002514047A Abandoned CA2514047A1 (en) | 2003-01-24 | 2004-01-23 | Spermicidal and/or antifungal composition and methods of using the same |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US7544696B2 (es) |
| EP (1) | EP1585732B1 (es) |
| JP (2) | JP4597136B2 (es) |
| KR (1) | KR20050103282A (es) |
| CN (1) | CN1751027A (es) |
| AT (1) | ATE499914T1 (es) |
| AU (1) | AU2004207436B2 (es) |
| BR (1) | BRPI0406572A (es) |
| CA (1) | CA2514047A1 (es) |
| CO (1) | CO5670353A2 (es) |
| DE (1) | DE602004031588D1 (es) |
| EC (1) | ECSP055992A (es) |
| ES (1) | ES2359814T3 (es) |
| IL (1) | IL169784A0 (es) |
| MX (1) | MXPA05007892A (es) |
| NO (1) | NO20053913L (es) |
| RU (1) | RU2346687C2 (es) |
| UA (1) | UA82864C2 (es) |
| WO (1) | WO2004066934A2 (es) |
| ZA (1) | ZA200505870B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7795436B2 (en) | 2005-08-24 | 2010-09-14 | Bristol-Myers Squibb Company | Substituted tricyclic heterocycles as serotonin receptor agonists and antagonists |
| AU2007240384A1 (en) * | 2006-04-19 | 2007-11-01 | Research Triangle Institute | Antispermatogenic, spermicidal and/or antifungal composition and methods of using the same |
| US20110237676A1 (en) * | 2007-08-21 | 2011-09-29 | Lehigh University | Spermicidal and microbicidal compositions |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2470108A (en) | 1949-05-17 | Heterocyclic amines | ||
| US2470109A (en) | 1949-05-17 | Heterocyclic amines | ||
| US2546652A (en) | 1949-07-30 | 1951-03-27 | Hoffmann La Roche | Pyridindenes and process for their manufacture |
| CH432518A (de) | 1964-01-17 | 1967-03-31 | Sandoz Ag | Verfahren zur Herstellung von neuen heterocyclischen Verbindungen |
| CH498120A (de) | 1968-03-28 | 1970-10-31 | Sandoz Ag | Verfahren zur Herstellung neuer Indenopyridinderivate |
| US3462443A (en) | 1967-04-19 | 1969-08-19 | Mcneilab Inc | Indeno(1,2-c)pyridine derivatives |
| DE77720C (de) | 1968-05-21 | FARBWERKE VORM. MEISTER LUCIUS & BRÜNING, Höchst a. M | Verfahren zur Darstellung eines grün bis schwarz färbenden Beizenfarbstoffs der Anthracenreihe | |
| GB1306404A (en) | 1969-05-07 | 1973-02-14 | Sandoz Ltd | Indenopyridine derivatives |
| US3627773A (en) | 1969-06-09 | 1971-12-14 | Sandoz Ltd | 1,3,4,4A,5,9B-HEXAHYDRO-5-PHENYL-2H-INDENO{8 1,2-c{9 -PYRIDINES |
| US3678057A (en) | 1970-03-26 | 1972-07-18 | Sandoz Ltd | 1,3,4,4A,5,9B-HEXAHYDRO-5-PHENYL-2H-INDENO{8 1,2-c{9 -PYRIDINES |
| US3991066A (en) | 1971-01-26 | 1976-11-09 | Sandoz Ltd. | 1,3,4,9B-Tetrahydro-5-methyl-2H-indeno[1,2-c]pyridines |
| US5314917A (en) * | 1991-03-22 | 1994-05-24 | E. B. Michaels Research Associates, Inc. | Method for inactivating enveloped viruses and sperm |
| US5319084A (en) * | 1993-08-16 | 1994-06-07 | Research Triangle Institute | Hexahydroindenopyridine compounds having antispermatogenic activity |
| US5952336A (en) * | 1997-01-31 | 1999-09-14 | Research Triangle Institute | Hexahydroindenopyridine compounds having antispermatogenic activity |
-
2003
- 2003-01-24 US US10/350,232 patent/US7544696B2/en not_active Expired - Fee Related
-
2004
- 2004-01-23 CN CNA2004800047483A patent/CN1751027A/zh active Pending
- 2004-01-23 ES ES04704789T patent/ES2359814T3/es not_active Expired - Lifetime
- 2004-01-23 AU AU2004207436A patent/AU2004207436B2/en not_active Ceased
- 2004-01-23 BR BR0406572-7A patent/BRPI0406572A/pt not_active IP Right Cessation
- 2004-01-23 RU RU2005126720/14A patent/RU2346687C2/ru not_active IP Right Cessation
- 2004-01-23 UA UAA200508141A patent/UA82864C2/uk unknown
- 2004-01-23 JP JP2006536504A patent/JP4597136B2/ja not_active Expired - Fee Related
- 2004-01-23 CA CA002514047A patent/CA2514047A1/en not_active Abandoned
- 2004-01-23 MX MXPA05007892A patent/MXPA05007892A/es not_active Application Discontinuation
- 2004-01-23 AT AT04704789T patent/ATE499914T1/de not_active IP Right Cessation
- 2004-01-23 DE DE602004031588T patent/DE602004031588D1/de not_active Expired - Lifetime
- 2004-01-23 EP EP04704789A patent/EP1585732B1/en not_active Expired - Lifetime
- 2004-01-23 KR KR1020057013691A patent/KR20050103282A/ko not_active Application Discontinuation
- 2004-01-23 ZA ZA200505870A patent/ZA200505870B/en unknown
- 2004-01-23 WO PCT/US2004/000206 patent/WO2004066934A2/en active Application Filing
-
2005
- 2005-07-20 IL IL169784A patent/IL169784A0/en unknown
- 2005-08-22 NO NO20053913A patent/NO20053913L/no not_active Application Discontinuation
- 2005-08-22 CO CO05083226A patent/CO5670353A2/es not_active Application Discontinuation
- 2005-08-31 EC EC2005005992A patent/ECSP055992A/es unknown
-
2008
- 2008-11-25 US US12/277,708 patent/US8193213B2/en not_active Expired - Fee Related
-
2010
- 2010-06-22 JP JP2010141878A patent/JP2010202671A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US8193213B2 (en) | 2012-06-05 |
| CN1751027A (zh) | 2006-03-22 |
| ATE499914T1 (de) | 2011-03-15 |
| US20040147539A1 (en) | 2004-07-29 |
| RU2346687C2 (ru) | 2009-02-20 |
| IL169784A0 (en) | 2007-07-04 |
| NO20053913L (no) | 2005-08-22 |
| US20090149490A1 (en) | 2009-06-11 |
| ZA200505870B (en) | 2006-10-25 |
| US7544696B2 (en) | 2009-06-09 |
| EP1585732A2 (en) | 2005-10-19 |
| CO5670353A2 (es) | 2006-08-31 |
| ECSP055992A (es) | 2006-01-16 |
| ES2359814T3 (es) | 2011-05-27 |
| JP2010202671A (ja) | 2010-09-16 |
| JP4597136B2 (ja) | 2010-12-15 |
| AU2004207436A1 (en) | 2004-08-12 |
| AU2004207436B2 (en) | 2009-08-06 |
| EP1585732A4 (en) | 2009-01-28 |
| BRPI0406572A (pt) | 2005-12-20 |
| UA82864C2 (en) | 2008-05-26 |
| JP2007506806A (ja) | 2007-03-22 |
| EP1585732B1 (en) | 2011-03-02 |
| DE602004031588D1 (de) | 2011-04-14 |
| WO2004066934A2 (en) | 2004-08-12 |
| WO2004066934A3 (en) | 2005-05-19 |
| MXPA05007892A (es) | 2005-11-17 |
| KR20050103282A (ko) | 2005-10-28 |
| RU2005126720A (ru) | 2006-02-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140506 |